


Letters to an Inmate

by lonewolfe707



Category: Supernatural
Genre: Alternate Universe - Prison, Letters, M/M, Other, Pen Pals
Language: English
Status: In-Progress
Published: 2016-01-19
Updated: 2017-04-15
Packaged: 2018-05-15 00:38:44
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 9
Words: 2,031
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5765035
Author URL: https://archiveofourown.org/users/lonewolfe707/pseuds/lonewolfe707
Summary: <blockquote class="userstuff">
              <p>College freshman Castiel Novak becomes inspired to write a letter to inmate Dean Winchester in an attempt to form a friendship.</p>
            </blockquote>





	1. Chapter 1

1/15/14

Dear Mr. Winchester,

My name is Castiel Novak. I was inspired by an organization called Beyond This Prison to write to you. I hope that is acceptable to you.  
I understand that you are in prison for murder. May I ask for details? It is alright if you do not wish to share.  
A little about me: I am a freshman at Saint Mary’s College of California. It resides in Moraga, California (the California part should be rather obvious). I am a Theology major. My family is extremely religious, so it seemed a good match.  
I have three siblings: Anael (she goes by Anna), Gabriel, and Michael. Anna is the only one who is younger than me, and Michael is the oldest. Gabriel and I are in the middle. Anna is still in high school, Gabriel is a sophomore studying Biochemistry at Stanford University, and Michael recently graduated from Harvard School of Law and is currently working as an attorney in Boston.  
What about you? How old are you? How long have you been incarcerated? Did you have any passions before you were incarcerated? Did you have any life goals?  
I await your response.

Sincerely yours,

Castiel Novak


	2. Chapter 2

1/21/14

Castiel-

Jeez. I haven’t gotten that level of formality in a long time.  
You seem like a good kid, Castiel. Makes me kind of glad I signed up for that prison pen pal thing. To be honest, I wasn’t really expecting that anyone would actually write to me.  
It’s true, I’m here for murder. I don’t really feel like going into detail. Just know that it was self-defense. I wouldn’t kill just for killing, or out of anger.  
You’re a college student? That’s good. Stay in school. I dropped out of high school as soon as I turned 18, and it was the biggest mistake of my life.  
Actually, probably not.  
Still, it was a big mistake.  
I honestly didn’t know you could major in Theology. I’ve never really been big on religion, or God in general. It’s cool that you are, though.  
I’ve been in prison since I was 20, and I’m 24 now, so I’ve been in here for 4 years. I wouldn’t really use the word passions, but I liked working on cars. I actually had thought about being a mechanic, before-  
You get the picture.  
You have quite a few siblings! I only have my younger brother, Sam. He’s 20 now, and he’s studying law at Stanford. Looks like he goes to school with your brother.  
Anyway, I guess I’ll be waiting for you to write back.

-Dean Winchester

(P.S. Mr. Winchester was my father, and I really don’t want to be associated with him, so call me Dean. Thanks.)


	3. Chapter 3

2/10/14

Dear Dean,

I apologize. It’s been 20 days since you wrote back to me. I’ve been rather busy with classes.  
I thank you for writing back. I am glad that we are able to correspond.  
You are incarcerated for self-defense? I am sorry. That must be difficult, knowing that you had no other options. Are you in jail for life? If not, how long are you in jail for?  
I asked Gabriel about your brother, and he says that he’s heard of him, but has never met him. He was interested enough to say he’s going to try and contact him.  
To be perfectly candid, I am not sure I want to continue majoring in Theology. Recent developments in my life have led me to question Christianity and the moral views it holds. To leave the major would raise questions within my family, though, and I’d rather not do that.  
You wish to be a mechanic? That’s an interesting goal. I’ve never gotten to know a mechanic, before. Is it difficult, not being able to do what you love in prison?  
I await your reply.

Sincerely yours,

Castiel Novak


	4. Chapter 4

2/15/14

Castiel-

It’s fine, man. I understand why you’d be writing a bit late. It’s good that you’re trying to get an education.  
And tell your brother that there’s no need to meet Sam. In fact, I’d prefer he didn’t. Sorry about that. I shouldn’t have mentioned that they go to the same school.  
I’m not incarcerated for life. I have a 10 year sentence, so I have 6 more years to go. Not bad, considering what I did.  
Oh, and if you don’t want to be a Theology major, then don’t be a Theology major. Screw your family. If they ask questions, just tell them that you wanted to try something else. What major do you want to take?  
I’m not going to ask about the “recent developments.” I figure it’s not my business, anyway. You can tell me if you want, but if you don’t, that’s fine, too.  
Yeah, being a mechanic was pretty much my only goal in life. My father wanted me to join the family business, but I never really wanted to. Working on cars was something I enjoyed, and it was easy for me. It’s too bad I’m here. It’s gonna be impossible to get a job when I get outta here, y’know?  
Anyway. Write back when you can, alright?

-Dean


	5. Chapter 5

2/17/14

Hey, Dean-o!

I hope you don’t mind that I’m writing to you- I bet you thought I was my brother when you opened this.  
Well, you get me instead. I’m Gabriel, Castiel’s big bro. I’m just writing to make sure you understand the predicament that you’re in.  
Your brother- who, by the way, is a total hottie- told me the truth about why you’re in there. A guy has to wonder- why lie about it to my brother? It kinda paints you as a hero, y’know?  
My brother’s smitten with you, by the way. I probably shouldn’t have told you that, but I figured you had a right to know. I don’t know how he can be so infatuated when you’ve only written him twice, but hey, Cassie’s weird.  
My point is, you need to come clean with him. I don’t appreciate people lying to my family, especially Castiel. He’s too innocent to see through your BS, but I can see it clearly.  
Stop being a dick, Dean-o.  
So glad we could have this chat!  
Make sure to write back!  
Or don’t. I honestly couldn’t give a shit.

Have a fantastic day,

Gabriel


	6. Chapter 6

2/19/14

Dear Dean,

I’m glad you understand. I tried to write back earlier this time, however.  
I apologize, but my brother has already met yours. He told me that Sam is a nice guy.  
I’m glad that you’re not incarcerated for life, and I’m excited that your sentence is almost half over. It must be hard, trying to get through this time in your life.  
I am confident that you will be able to find a job. If you explain that your murder was in self-defense, I’m sure that they will have no qualms in hiring you.  
As for my major, I’m not sure you understand how my parents would react to me changing my major. They might stop funding my college education, and I would be forced to leave my school.  
If I could choose any major, however, I would choose an English major. I always loved to read. It kept me entertained, as I didn’t have very many friends growing up. Reading gave me adventures to go on, adventures I could never have in the real world.  
Do you like to read? If so, what are your favorite books and authors? What genre do you normally read?  
I await your reply.

Sincerely yours,

Castiel Novak


	7. Chapter 7

2/27/14

Cas-

Do you mind if I call you that? I prefer Cas to Castiel.  
We need to talk.  
I may have misled you a bit. The murder I committed? I lied. It wasn’t in self defense.  
I mean, from certain angles, it was. But from other angles, it wasn’t.  
I killed my goddamn father, Cas.  
Sure, he was an abusive bastard, but he was my father.  
I came in one day, saw him yelling at Sam, saw him raise the bottle, ready to smash it on my brother’s head, and I lost it.  
I don’t really remember what happened next. All I know is that my father ended up on the floor, bleeding slowly to death.  
I’m sorry, Cas.  
I’m a piece of shit.  
A monster.  
You seem like a good kid, and I really don’t want to corrupt you.  
I won’t be writing back anymore.

-Dean

**Notes for the Chapter:**

> Note: This isn't the end of the story. Hopefully, I'll be adding more. I won't have time for a bit, my next term starts soon. I'll add more when I can!


	8. Chapter 8

4/12/14  
Dear Dean,

I am sorry that I did not reply for some time. I have had quite a bit of conflict in my life recently, and I felt that I should wait for things to settle before responding.  
Before I continue, I should mention that I don’t believe you did anything wrong. I understand your guilt, but I think you would have felt much guiltier if you had let your father continue to hurt your brother. Life can have a lot of hard decisions, but I personally believe that you made the most moral choice you could.  
I doubt my family would agree, but it seems as though we don’t agree on much these days. I was excommunicated yesterday, for lack of a better word. My brother Gabriel is allowing me to move in with him for the time being. The new address is the return address on this letter.  
I am truly sorry for what you have gone through, Dean. You don’t seem like a monster to me. In fact, if you were one, I doubt you would feel the guilt you are experiencing. Whatever the case, you seem like a good, righteous man, who doesn’t deserve what you’ve been put through.  
You may not see a future for yourself outside of prison, but I believe that there is one waiting for you. I hope you can believe that, as well.  
As always, I await your reply.

Sincerely yours, no matter what,

Castiel Novak

(P.S. I do not mind if you call me Cas. Also, I have included a copy of my favorite book. It’s my only copy, but I thought you might enjoy it, provided the prison staff allows you to read it.)

**Notes for the Chapter:**

> Hey guys! I'm really sorry I haven't updated in a while. I honestly had intended to, but just like Cas, I've also had some conflict in my life over the past year, and have been uprooted a bit in a different sense, I guess. But now that things are all settled, I wrote this chapter and the one after it, and will hopefully continue to update. Thank you all so much for waiting, I'm sorry it took so long.


	9. Chapter 9

Cas-

I don’t know how the hell you want to respond to that, man. I mean, you’re wrong about me, but it’s nice to have a vote of confidence, I guess.  
I’m sorry to hear about your family. I know you had the whole thing with the major, but I think I can guess what the other part of it was, from what your brother told me. I have some experience in the area and I really am sorry that you’re going through this right now. It’s a bunch of bullshit, but at least they can’t control you as much now.  
You’re living with Gabriel, which I guess means you’ve met Sammy. Tell him I say hi, and that he should write more. And tell your brother that he can be a bit less of a dick when he tells me what I already know.  
Oh, and by the way, I don’t really understand your whole logic on the monster guilt thing, but something tells me I won’t be able to persuade you otherwise, so I’ll just let you think what you want. It’s nice to have someone to talk to, anyway. Might as well try not to ruin it.  
It’s nice that you see a future for me, too, I guess. I’m not sure what the hell I’ll be doing once I’m out of here, and I don’t exactly put much faith in hope, but it’s a nice sentiment. I appreciate it.  
You know, it’s funny. I’d convinced myself I didn’t want you to respond, but I’m happy you did. I hope you do again.  
Have a good one.

-Dean

(P.S. They’re letting me read the book you sent. I’m gonna be honest, I understand about half of what I’ve read, and I’ve only made it to Chapter 4. But I’m gonna keep going. Who knows, maybe Chapter 5 is where it starts making sense.)


End file.
